Photo by Robbie Martin

Upton Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Upton

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (56)
"This house was a blast - would def stay again"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Newly built cedar Log Home overlooking Rangeley Lake with views galore

10.0 out of 10, Exceptional, (3)
"Beautiful views of the lake and peaceful surroundings"
Newly built cedar Log Home overlooking Rangeley Lake with views galore

NEW* Lakefront Escape; Sleeps12, hottub, gameroom & UTV, Direct Snowmobile

10.0 out of 10, Exceptional, (9)
"We had the best time! It is a beautiful property and there is SO much space. We hope to be back for a ski weekend at Saddleback in the future!! "
NEW* Lakefront Escape; Sleeps12, hottub, gameroom & UTV, Direct Snowmobile

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (90)
"Had a wonderful stay Rediker retreat. Truly a retreat. The property had everything we needed for our holiday week. Thanks for having us. "
Rediker Retreat- Authentic Riverfront Luxury Log Home

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (28)
"Great place, great location, great amenities, thanks for the great stay!"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

3 Bedroom cabin on South Pond in Stark NH

2.0 star property
10.0 out of 10, Exceptional, (10)
"Great place.. very clean.. near hiking spots"
3 Bedroom cabin on South Pond in Stark NH

4-Season Rangeley Cabin - Wood Stove, Water Views, Fiber Internet, Game Room

10.0 out of 10, Exceptional, (24)
"Everything about our stay was absolutely great. The house is gorgeous, spacious, and clean, not to mention well-stocked and very easy to find. Amanda was communicative and helpful, and we enjoyed our visit so much. Hope to make it back in the future!"
4-Season Rangeley Cabin - Wood Stove, Water Views, Fiber Internet, Game Room

Panoramic Water and Mountains Views with Nature appearing daily. Relax on

10.0 out of 10, Exceptional, (55)
"My kids loved the beach a short walk away, and the shallow water was crystal clear. Because of the location, there really is a view from every window. Kind of small cabin and lot though"
Panoramic Water and Mountains Views with Nature appearing daily. Relax on

🐾Eagles Ledge | Cozy chalet w/ incredible views, access to Rangeley Lake & 15 mins to Saddleback!

9.2 out of 10, Wonderful, (51)
"We’ve enjoyed Eagles Ledge for a couple years now and love everything about it."
🐾Eagles Ledge | Cozy chalet w/ incredible views, access to Rangeley Lake & 15 mins to Saddleback!

Safety Certified luxury private, dog-friendly new home, 3 miles to Sunday River.

10.0 out of 10, Exceptional, (12)
"Cozy , fresh air , perfect place for the family and the kid Highly recommend,"
The price is NZ$1,667
includes taxes & fees
11 Sept - 12 Sept
Safety Certified luxury private, dog-friendly new home, 3 miles to Sunday River.

ATV and Snowmobile right from the house !!!!

9.0 out of 10, Wonderful, (59)
"My family and i have had the pleasure of staying here a few times and we love where the house is and being able to walk to the park with the kids. They have had a lot of fun there. Bedrooms were perfect, plenty of beds and space. Loved our stay."
The price is NZ$387
includes taxes & fees
18 Aug - 19 Aug
ATV and Snowmobile right from the house !!!!

Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

8.8 out of 10, Excellent, (39)
"Great views and location if you are looking for a part of Maine not super coastal and touristy."
Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

10.0 out of 10, Exceptional, (323)
"Great place!"
The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

Hike, fish, bike, float the river, explore or just relax...

9.4 out of 10, Exceptional, (23)
"The house is exactly as pictured. It's clean, airy, great view of the slopes from the huge windows in the living room! Kitchen has the core things you need. Kids really enjoyed the basement couch area. Host was super responsive and accommodating. Highly recommend!!"
Hike, fish, bike, float the river, explore or just relax...

Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

10.0 out of 10, Exceptional, (120)
"Nice comfortable stay near Sunday River. Worked great for two families staying for the weekend. "
Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

90 Second, Traffic-Free Drive to Sunday River

10.0 out of 10, Exceptional, (20)
"Beautiful, clean, comfortable home conveniently located near Sunday River. "
The price is NZ$1,144
includes taxes & fees
1 Sept - 2 Sept
90 Second, Traffic-Free Drive to Sunday River

Lakefront Cabin - dock, beach, sauna, and views!

9.8 out of 10, Exceptional, (27)
"Great overall experience and very friendly / helpful hosts. Would recommend."
Lakefront Cabin - dock, beach, sauna, and views!

Cozy Cabin on Rangeley Lake

10.0 out of 10, Exceptional, (14)
"Kitchen is very well stocked and property is very clean. Close to everything in Rangeley and right on the lake. "
Cozy Cabin on Rangeley Lake

Ski-in/out, dog-friendly townhome with mountain views, hot tub & pool

9.6 out of 10, Exceptional, (17)
"We had a great time and the condo is beautiful! "
Ski-in/out, dog-friendly townhome with mountain views, hot tub & pool

Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise

10.0 out of 10, Exceptional, (23)
"This was our second time staying here. The house is so cozy, with big windows looking out over the lake. The kitchen is well stocked, beds are comfortable, and I love the towel warmer in the bathroom. "
Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Upton Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Upton?

Yes, there are holiday rentals close to the most popular sights in Upton, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Upton has to offer?

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space: This holiday home rental outside of Upton is located on a river, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Upton?

While you're exploring the area, Lake Umbagog and Magalloway River are a couple of picturesque spots to get outside and enjoy nature. Umbagog State Park and Upton Public Library are other places to visit while you're in town.

What are holiday rentals like in Upton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upton. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.